Process for preparing food products containing cocoa polyphenols

ABSTRACT

The invention provides food products, including confectioneries and chocolates, having conserved concentrations of polyphenols, and in particular cocoa polyphenols. The method of this invention avoids the significant and detrimental losses of polyphenols that occur during conventional manufacture by controlling the handling of ingredients in batching processing to provide a product having a significant amount of the cocoa polyphenol concentration present in the raw materials conserved in the finished product. Additionally, the production steps of milling/refining and conching may also be controlled and modified to provide the confectioneries of the present invention having conserved concentrations of cocoa polyphenols relative to the concentration of the polyphenols present in the starting ingredients. The cocoa polyphenol ingredient may be a cocoa ingredient, an extract of a cocoa ingredient (beans, liquor, or powder, etc.) or may be a synthesized derivative thereof, or may be a synthesized polyphenol compound or mixture of polyphenol compounds or derivative thereof.

This application is a continuation-in-part of International ApplicationNo. PCT/US97/15893, field Sep. 8, 1997 which was a continuation in partof U.S. Application Ser. No. 08/709,406, filed Sep. 6, 1996, now U.S.Pat. No. 6,015,913.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention relates to food products having a conserved or enhancedcontent of cocoa polyphenols and processes for producing the same. Thefood products prepared by the processes of this invention include ediblefood products, confectionery products and standard of identity andnon-standard of identity chocolate products, and the like, havingconserved concentrations of cocoa polyphenols therein.

2. Related Background Art

Polyphenolic compounds are bioactive substances that are derived fromplant materials and are closely associated with the sensory andnutritional quality of products derived from these plant materials. Theterm “cocoa polyphenol” includes the polyphenolic products, includingproanthocyanidins, and more particularly procyanidins, extracted fromcocoa beans and derivatives thereof. More specifically, the term “cocoapolyphenol” includes monomers of the formula A_(n) (where n is 1) oroligomers of the formula A_(n) (where n is an integer from 2 to 18, andhigher), wherein A has the formula:

and R is 3-(α)—OH, 3-(β)—OH, 3-(α)—O-saccharide, 3-(β)—O-saccharide,3-(α)—O—C(O)—R′, or 3-(β)—O—C(O)—R′;

bonding between adjacent monomers takes place at positions 4, 6 or 8;

a bond to a monomer in position 4 has alpha or beta stereochemistry;

X, Y and Z are selected from the group consisting of A, hydrogen, and asaccharide moiety, with the provisos that as to at least one terminalmonomer, bonding of the adjacent monomer thereto is at position 4 andoptionally Y═Z═hydrogen; and

wherein the saccharide moiety is a mono- or di-saccharide moiety and maybe optionally substituted with a phenolic moiety and R′ may be an arylor heteroaryl moiety optionally substituted with at least one hydroxylgroup; and

salts, derivatives and oxidation products thereof.

Advantageously, the saccharide moiety is derived from the groupconsisting of glucose, galactose, xylose, rhamnose and arabinose. Thesaccharide moiety and any or all of R, X, Y, and Z may optionally besubstituted at any position with a phenolic moiety via an ester bond.The phenolic moiety is selected from the group consisting of caffeic,cinnamic, coumaric, ferulic, gallic, hydroxybenzoic and sinapic acids.

Many plant polyphenols have antioxidant activity and have an inhibitoryeffect on mutagenesis and carcinogenesis. Cocoa polyphenol extracts,particularly procyanidins, have recently been shown to possesssignificant biological utility. Particularly, WO 97/36497 discloses thatthese extracts also function to reduce periodontal disease,atherosclerosis and hypertension, inhibit LDL oxidation and DNAtopoisomerase II, modulate cyclo-oxygenase, lipoxygenase, nitric oxideor NO-synthase, apoptosis, platelet aggregation, and possessanti-inflammatory, antigingivitis and antiperiodontis activity.Moreover, WO 97/36497 discloses that oligomers 5-12 possess the highestanti-cancer activity of the polyphenolic compounds isolated from cocoa.Thus, consumption of these higher oligomers in cocoa products mayprovide significant health benefits. Accordingly, food products, such asconfectioneries and cocoa-containing products (cocoa powders, chocolateliquors, or extracts thereof) having a high cocoa polyphenolconcentration, especially a high concentration of cocoa polyphenololigomers 5-12, would be especially desirable.

The cocoa polyphenol extracts, or compounds further separated therefrom,have generally been prepared, on a laboratory scale, by reducing cocoabeans to a powder, defatting the powder, and extracting and purifyingthe active compound(s) from the defatted powder. The powder is generallyprepared by freeze-drying the cocoa beans and pulp, de-pulping andde-shelling the freeze-dried beans and grinding the de-shelled beans ornibs. The extraction of active compound(s) has been accomplished bysolvent extraction techniques, and the extracts have been purified bygel permeation chromatography, preparative high performance liquidchromatography (HPLC) techniques, or by a combination of such methods,as disclosed in Romanczyk et al., U.S. Pat. No. 5,554,645.

Under-fermented and unfermented cocoa raw materials contain substantialamounts of cocoa polyphenols, compared to fermented cocoa. Fermentationand drying bring about complex changes in the cocoa bean, most notably,the formation of components required for the development of thecharacteristic flavor and color of cocoa. Fermentation, however, alsosignificantly decreases the concentrations of polyphenolic compounds inthe fermented cocoa beans, relative to the concentrations ofpolyphenolic compounds in unfermented or under-fermented beans.Traditional cocoa bean processing, including such steps as roasting orde-fatting of the cocoa beans, also reduces the cocoa polyphenolconcentration in the cocoa powder or chocolate liquors produced thereby.Moreover, these processes reduce the concentrations of higher oligomericpolyphenols (oligomers 5-12) more rapidly than lower oligomers (2-4) ormonomers. Accordingly, it was highly desirable to develop methods ofconserving or retaining the higher oligomers that not only possessedmore significant biological activity than lower oligomers, but alsoappeared to be more sensitive to processing conditions than the loweroligomers.

Accordingly, it would be highly desirable to develop processingtechniques to prepare food products and confectioneries, particularlycocoa-containing confectioneries, that will conserve the cocoapolyphenol concentration of cocoa powders, chocolate liquors, orextracts thereof, in the finished, shelf-ready product.

SUMMARY OF THE INVENTION

The invention relates to novel food products, and their process ofproduction, containing a conserved or enhanced concentration ofpolyphenols. In a preferred embodiment, the invention provides processesfor producing confectionery products, including standard of identity andnon-standard of identity chocolate products, having conservedconcentrations of polyphenols, and preferably cocoa polyphenols, andmore preferably cocoa polyphenol oligomers. The process of the presentinvention comprises:

(a) mixing at least one ingredient of the product with at least onepolyphenol-conserving pre-treatment ingredient to form a mix,

(b) combining the mix with at least one ingredient containing cocoapolyphenol, and

(c) forming the polyphenol-containing product, wherein the productcontains at least about 10% by weight more polyphenol than a productprepared without using the pre-treatment process according to step (a).

The process of this invention avoids the significant and detrimentallosses of polyphenols that occur during conventional manufacture. Thisinvention provides novel food products prepared frompolyphenol-containing ingredients that may be cocoa ingredients,extracts of a cocoa material (beans, liquor, or powder, etc.) or may bea synthesized derivative thereof, or may be synthesized polyphenolcompounds or a mixture of polyphenol compounds or derivative thereof.Mixing ingredients in a specific order provides a product having asignificant amount of the cocoa polyphenol concentration, present in theraw materials, conserved in the finished product. Additionally, theproduction steps of milling/refining and conching may also be controlledand modified to provide the confectioneries of the present inventionhaving conserved concentrations of cocoa polyphenols. Thus, theinvention relates to processes of obtaining food products andconfectioneries having a conserved concentration of cocoa polyphenolsrelative to the starting ingredients. The invention avoids thesignificant and detrimental losses of cocoa polyphenols that occurduring conventional manufacture.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1(a)-(d) illustrate the change in the surface of the cut bean halfduring the fermentation of the cocoa bean FIG. 1(a) depicts the cut beanof an unfermented cocoa bean; FIGS. 1(b)-(d) depict the cocoa bean as itis fermented, with FIG. 1(d) illustrating the fully fermented cocoabean.

DETAILED DESCRIPTION OF THE INVENTION

It has now been determined that the retention of polyphenols, andparticularly higher oligomeric (5-12) polyphenols, in food products isdependent upon the order of addition of ingredients during batchprocessing. Polyphenols are known to complex with proteins, alkaloids,metal cations and carbohydrates. Without being bound to theory, it isbelieved that the processes of this invention prevent or reduce theadverse interactions between the polyphenol-containing ingredients andthe protein-containing and/or carbohydrate-containing ingredients usedtherein. The processes of the present invention provide finished,shelf-ready food products with conserved concentration of the cocoapolyphenols present in the polyphenol-containing ingredients used toprepare the food products. More preferably, the processes of the presentinvention provide finished, shelf-ready confectionery products withconserved concentration of cocoa polyphenol oligomers 5-12. Theconcentration of cocoa polyphenol pentamer (polyphenol oligomer 5), inthe resulting products of the present invention, was used as anindicator of the effectiveness of cocoa polyphenol conservation in theprocesses of the invention.

The process of preparing a food product according to this inventioncomprises:

(a) mixing at least one ingredient of the product with at least onepolyphenol-conserving pre-treatment ingredient to form a mix,

(b) combining the mix with at least one ingredient containing cocoapolyphenol, and

(c) forming the polyphenol-containing food product, wherein the productcontains at least about 10% by weight more polyphenol than a productprepared without using the pre-treatment process according to step (a).

Additional ingredients desired in the resulting food product may beadded at any point in the process.

As used herein, the term “food product” includes any edible product,including foods, confectioneries, and diet supplements, particularlycocoa-containing foods, confectioneries, and diet supplements.Confectioneries refer to any sweetened foods, particularly candy,chocolate, icings and the like.

The term “cocoa polyphenol” includes the procyanidins present in cocoabeans or a cocoa ingredient used in the production of confectioneryproducts, chocolate confectioneries and chocolate products, extracts ofcocoa beans or a cocoa ingredient comprising procyanidins, andsynthesized derivatives thereof, and includes synthesized cocoapolyphenol compounds or synthesized mixtures of polyphenol compounds,and derivatives thereof. The term “cocoa ingredient” refers to a cocoasolids-containing material derived from shell-free cocoa nib andincludes chocolate liquor and partially or fully defatted cocoa solids(e.g., cake or powder), alkalized cocoa powder or alkalized chocolateliquor and the like. The term “chocolate liquor” refers to the darkbrown fluid “liquor” formed by grinding a cocoa nib. The fluidity is dueto the breakdown of the cell walls and the release of the cocoa butterduring the Processing resulting in a suspension of ground particles ofcocoa solids suspended in cocoa butter.

Preferred chocolate liquors include those from underfermented beansbecause the beans have a higher cocoa polyphenol content.

The cocoa polyphenol oligomers may be prepared by:

(a) protecting each phenolic hydroxyl group of a first and a secondpolyphenol monomer with a protecting group to produce a first and asecond protected polyphenol monomer;

(b) functionalizing the 4-position of the first protected polyphenolmonomer to produce a functionalized protected polyphenol monomer havingthe formula:

where c is 1 to 3, d is 1 to 4, y is 2 to 6, R is a protecting group,and R is H or OH;

(c) coupling the second protected polyphenol monomer with thefunctionalized protected polyphenol monomer to produce a protectedpolyphenol dimer;

(d) optionally repeating the protecting, functionalizing, and couplingsteps to form polyphenol oligomers having n monomeric units, where n isan integer from 3 to 18, preferably 5-12; and

(e) removing the protecting groups from the phenolic hydroxyl groups.

The preferred protected polyphenol monomer is a brominated protectedepicatechin or brominated protected catechin, e.g., 6, 8,6′-tribromo-epicatechin or a 6, 8, 6′-tribromo-catechin.

In the above process, the 4-position of the protected polyphenol monomermay be oxidatively functionalized using a quinone oxidizing agent in thepresence of a diol, e.g., ethylene glycol, in which case y is 2.

The above process may further comprise the step of forming a derivativeof the polyphenol oligomer by esterifying the polyphenol oligomer at the3-position of at least one monomeric unit to produce an esterifiedpolyphenol oligomer. The ester group may be selected from the groupconsisting of —OC(O)-aryl, —OC(O)-substituted aryl, —OC(O)-styryl, andOC(O)-substituted styryl, where the substituted aryl or substitutedstyryl group contains at least one substituent selected from the groupconsisting of halo, hydroxyl, nitro, cyano, amino, thiol,methylenedioxy, dihalomethylenedioxy, a C₁-C₆ alkyl, a C₁-C₆ alkoxy, aC₁-C₆ haloalkyl, a C₁-C₆ haloalkoxy, a C₃-C₈ cycloalkyl, and a C₃-C₈cycloalkoxy. Preferably, the 3-position of at least one monomeric unitis converted to a derivative group derived from an acid selected fromthe group consisting of caffeic, cinnamic, coumaric, ferulic, gallic,hydroxybenzoic and sinapic acids.

The above process may further comprise the step of forming a derivativeof the polyphenol oligomer by glycosylating the polyphenol oligomer atthe 3-position of at least one monomeric unit to produce a glycosylatedpolyphenol oligomer. Preferably, the 3-position of at least onemonomeric unit is converted to a derivative group selected from thegroup consisting of a —O-glycoside and an —O-substituted glycosidewherein the substituted glycoside is substituted by —C(O) aryl,—C(O)-substituted aryl, —C(O)-styryl, or —C(O)-substituted styrylgroups. The substituted aryl or substituted styryl group may containsubstituents selected from the group consisting of halo, hydroxyl,nitro, cyano, amino, thiol, methylenedioxy, dihalomethylenedioxy, aC₁-C₆ alkyl, a C₁-C₆ alkoxy, a C₁-C₆ haloalkyl, a C₁-C₆ haloalkoxy, aC₃-C₈ cycloalkyl and a C₃-C₈ cycloalkoxy. Preferably, the glycoside isderived from the group consisting of glucose, galactose, xylose,rhamnose, and arabinose structurally represented as oligomers of monomerA, having the formula A_(n), where n is 2-18, wherein A has the formula:

and R is 3-(α)—OH, 3-(β)—OH, 3-(α)—O-saccharide, 3-(β)—O-saccharide;

bonding between adjacent monomers takes place at positions 4, 6 or 8;

a bond to a monomer in position 4 has alpha or beta stereochemistry;

X, Y and Z are selected from the group consisting of A, hydrogen, and asaccharide moiety, with the provisos that as to at least one terminalmonomer, bonding of the adjacent monomer thereto is at position 4 andoptionally Y═Z═hydrogen; and

salts thereof;

wherein the saccharide moiety is derived from a mono- or di-saccharide.

Synthesized derivatives of the cocoa polyphenols include compounds,according to the structure A_(n), above, wherein R may be3-(α)—O-saccharide, 3-(β)—O-saccharide, 3-(α)—O—C(O)—R′, or3-(β)—O—C(O)—R′, wherein the saccharide moiety may be derived from amono- or di-saccharide selected from the group consisting of glucose,galactose, xylose, rhamnose and arabinose; the saccharide moiety of anyor all of R, X, Y, and Z may be optionally substituted at any positionwith a phenolic moiety via an ester bond; the phenolic moiety may beselected from the group consisting of caffeic, cinnamic, coumaric,ferulic, gallic, hydroxybenzoic and sinapic acids; and R′ is an aryl orheteroaryl moiety optionally substituted with at least one hydroxylgroup. The substituted aryl or heteroaryl moiety of R′ may preferablycontain a substitution pattern corresponding to the substituted phenolicmoieties of caffeic, cinnamic, coumaric, ferulic, gallic, hydroxybenzoicor sinapic acids.

Partially defatted cocoa solids having a high cocoa polyphenol (CP)content, i.e., a high cocoa procyanidin content, can be obtained byprocessing the cocoa beans directly to cocoa solids without a bean ornib roasting step as disclosed in U.S. Pat. No. 6,015,913 issued Jan.18, 2000 to K. Kealy et al., the disclosure of which is incoporatedherein by reference. This method conserves the cocoa polyphenols becauseit omits the traditional roasting step. The method comprises the stepsof: (a) heating the cocoa beans to an internal bean temperature justsufficient to reduce the moisture content to about 3% by weight and toloosen the cocoa shell; (b) winnowing the cocoa nibs from the cocoashells; (c) screw pressing the cocoa nibs; and (d) recovering the cocoabutter and partially defatted cocoa solids which contain cocoapolyphenols including cocoa procyanidins.

Optionally, the cocoa beans are cleaned prior to the heating step, e.g.,in an air fluidized bed density separator. The winnowing can also becarried out in a air fluidized bed density separator. Preferably, thecocoa beans are heated to an internal bean temperature of about 100° C.to about 110° C., more preferably less than about 105° C., typicallyusing a infra red heating apparatus for about 3 to 4 minutes If desired,the cocoa solids can be alkalized and/or be milled to a cocoa powder.

The internal bean temperature (IBT) can be measured by filling aninsulated container such as a thermos bottle with beans (approximately80-100 beans). The insulated container is then appropriately sealed inorder to maintain the temperature of the sample therein. A thermometeris inserted into the bean-filled insulated container and the temperatureof the thermometer is equilibrated with respect to the beans in thethermos. The temperature reading is the IBT temperature of the beans.IBT can also be considered the equilibrium mass temperature of thebeans.

Cocoa beans can be divided into four categories based on their color:predominately brown (fully fermented), purple/brown, purple, and slaty(underfermented). Preferably, the cocoa solids are prepared fromunderfermented cocoa beans, i.e., slaty cocoa beans, purple cocoa beans,mixtures of slaty and purple cocoa beans, mixtures of purple and browncocoa beans, or mixture of slaty, purple, and brown cocoa beans. Morepreferably, the cocoa beans are slaty and/or purple cocoa beans whichhave a higher cocoa polyphenol content than fermented beans.

The cocoa polyphenols, including the cocoa procyanidins, may be solventextracted from the partially defatted cocoa solids prepared from theunroasted cocoa beans. The cocoa procyanidin oligomers identified in theextract include the dimer to the nonamer.

The partially defatted cocoa solids and/or cocoa polyphenol extracts canbe used in therapeutic compositions, optionally with a carrier or adiluent. The therapeutic compositions are useful as antineoplasticcompositions, antioxidants, antimicrobial agents, nitric oxide (NO) orNO-synthase modulators, cyclo-oxygenase modulators, lipoxygenasemodulators, and in vivo glucose modulators.

The cocoa polyphenol (CP) content, including the cocoa procyanidincontent, is higher when underfermented cocoa beans or blends thereof afermentation factor of 275 or less, are selected for processing into thecocoa components,

The “fermentation factor” is determined using a grading system forcharacterizing the fermentation of the cocoa beans. Slaty is designated1, purple is 2, purple/brown is 3, and brown is 4. The percentage ofbeans falling within each category is multiplied by the weighted number.Thus, the “fermentation factor” for a sample of 100% brown beans wouldbe 100×4 or 400, whereas for a 100% sample of purple beans it would be100×2 or 200. A sample of 50% slaty beans and 50% purple beans wouldhave a fermentation factor of 150 [(50×1)+(50×2)].

The high CP chocolate liquor and/or high CP cocoa solids are preparedby: (a) roasting the selected cocoa beans (fermentation factor of 275 orless) to an internal bean temperature of 95° C. to 160° C.; (b)winnowing the cocoa nibs from the roasted cocoa beans; (c) milling thecocoa nibs into the chocolate liquor; and (d) optionally recoveringcocoa butter and partially defatted cocoa solids from the chocolateliquor. Alternatively, the chocolate liquor and/or cocoa solids can beprepared by: (a) heating the selected cocoa beans (fermentation factorof 275 or less) to an internal bean temperature of 95-135° C. to loosenthe cocoa shell from the cocoa nibs; (b) winnowing the cocoa nibs fromthe cocoa shells; (c) roasting the cocoa nibs to an internal nibtemperature of 95° C. to 160° C.; (d) milling the roasted nibs into thechocolate liquor; and (e) optionally recovering cocoa butter andpartially defatted cocoa solids from the chocolate liquor. Chocolateliquor and partially defatted cocoa solids containing at least 50,000 μgof total cocoa procyanidins and/or at least 5,000 μg of cocoaprocyanidin pentamer per gram of nonfat cocoa solids can be prepared bythe above processes.

An extract containing cocoa polyphenols including cocoa procyanidins canbe prepared by solvent extracting the partially defatted cocoa solids ornonfat cocoa solids prepared from the roasted underfermented cocoa beansor cocoa nibs.

High CP food products may be prepared using the high CP roasted cocoanibs, high CP chocolate liquors, and/or high CP partially defatted ornonfat cocoa solids. The food products include pet food, dry cocoamixes, puddings, syrups, cookies, savory sauces, rice mixes, and ricecakes. Preferably, the food products are confectioneries, e.g., a darkchocolate or a milk chocolate. The extract can also be used to preparefoods having high cocoa polyphenol contents.

The health of a mammal can be improved by administering to the mammal acomposition containing cocoa procyanidins or the above high CP cocoacomponents. In these compositions the total amount of the cocoaprocyanidin oligomers is at least 1 μg or greater and the composition isadministered daily over greater than 60 days.

The food products of this invention may contain one or more of the cocoapolyphenol monomers, oligomers 2-18, or derivatives thereof. Preferably,the food products of this invention contain mixtures cocoa polyphenololigomers 2-18, or derivatives thereof; more preferably, the foodproducts contain mixtures of cocoa polyphenol oligomers 5-12, orderivatives thereof.

The term “oligomer”, as used herein, refers to any compound of theformula presented above, wherein n is 2 through 18, and preferably,wherein n is 5-12. When n is 2, the oligomer is termed a “dimer”; when nis 3, the oligomer is termed a “trimer”; when n is 4, the oligomer istermed a “tetramer”; when n is 5, the oligomer is termed a “pentamer”;and similar recitations may be designated for oligomers having n up toand including 18 and higher, such that when n is 18, the oligomer istermed an “octadecamer”.

A “pre-treatment ingredient” is any ingredient that may be used in foodproducts, confectionery products and/or chocolate products thatfunctions to conserve and/or retain the cocoa polyphenol concentrationof any cocoa polyphenol-containing ingredient used therein. Preferably,the pre-treatment ingredient is any ingredient that may be used in foodproducts, especially confectionery products and/or chocolate products,that functions to conserve and/or retain the concentration of cocoapolyphenol oligomers 5-12 of any ingredient containing such oligomers.The pre-treatment ingredient demonstrates an activity that preventsreaction, complexation, decomposition or adverse interaction of cocoapolyphenols with any of the other ingredients or apparatus used in thepreparation of such products or with any polyphenol-reactive materialgenerated from or by the other ingredients during the preparation of theproducts. An example of a reactive material that may be generated fromor by other ingredients during the preparation of these food products isa free-radical reactive intermediate species. The pre-treatmentingredients may function to prevent the formation of polyphenol-reactivematerials or interact with polyphenol-reactive materials, therebypreserving the cocoa-polyphenol concentration of the cocoapolyphenol-containing ingredient in the products. Exemplarypre-treatment ingredients that may be used in the food products of thisinvention include water, fats, emulsifying agents, cocoa ingredients,antioxidant compounds, flavoring agents, other polyphenol-containingingredients, and the like.

The term “fat” as used herein, refers to triglycerides typcially used infood products, especially confectionery products and chocolate products.Fats useful in this invention include the naturally occurring fats andoils such as cocoa butter, pressed cocoa butter, expeller cocoa butter,solvent extracted cocoa butter, refined cocoa butter, milk fat,anhydrous milk fat, fractionated milk fat, milk fat replacers,butterfat, fractionated butterfat, and other vegetable fat, as well asother modifications of these fats, including cocoa butter equivalents(CBE), cocoa butter substitutes (CBS), cocoa butter replacers (CBR),anti-blooming agents, such as behenoyl oleoyl behenate (BOB), reducedcalorie fats and/or synthetically modified fats, including reducedcalorie fats and non-caloric fat substitutes. A reduced calorie fat is afat having all the properties of typical fat but having fewer caloriesthan typical fat. A non-caloric fat substitute, e.g. a sucrosepolyester, likewise possesses all the typical fat characteristics, butis not absorbed after ingestion and thus is not metabolized. To besuitable for use as a pre-treatment ingredient in this invention, thefat must not demonstrate an activity that promotes reaction,decomposition or adverse interaction of cocoa polyphenols. Fats that arehighly unsaturated are considered unsuitable for use as pre-treatmentingredients because these fats may generate free-radical species duringprocessing. Accordingly, fats and fatty acids having relatively highlevels of unsaturation, such as linoleic and linolenic acids, areconsidered unsuitable as polyphenol-conserving pre-treatmentingredients. Cocoa butter and fats obtained from genetically modifiedseed oils or modified seed oils having relatively low levels ofunsaturation, e.g. high oleic sunflower oil or high oleic peanut oilwould be especially preferred polyphenol-conserving pre-treatmentingredients.

Emulsifying agents, or emulsifiers, are also used as ingredients in thefood products of the present invention. Emulsifying agents are wellknown to play a critical role in suspension rheology and are usedthroughout food manufacturing, especially confectionery and chocolatemanufacturing, to enhance the rheology (i.e., reduce viscosity and/oryield value) of solids suspensions. Soy lecithin is one of the oldestand most widely used emulsifying agent. In chocolate, lecithindemonstrates a significant viscosity lowering effect when used at anoptimum concentration of about 0.3% to about 0.7% by weight of thefinished chocolate. Exemplary emulsifying agents useful in the presentinvention may be any of those emulsifying agents typically used in theart and include lecithin derived from vegetable sources such as soybean,safflower, corn, etc., fractionated lecithins, mono- and di-gylcerides,di-acetyl tartaric acid esters of mono- and di-glycerides (also referredto as DATEM), monosodium phosphate derivatives of mono- anddi-glycerides of edible fats or oils, sorbitan monostearate,polyoxyethylene sorbitan monostearate, hydroxylated lecithin, lactylatedfatty acid esters of glycerol and propylene glycol, polyglycerol estersof fatty acids, propylene glycol mono- and di-esters of fats and fattyacids, and especially any emulsifying agents that may become approvedfor the U.S. Food and Drug Administration-defined soft candy category.It is considered within the skill of one in the art to select anemulsifying agent for use in the preparation of a food product of thepresent invention. In addition, other emulsifying agents that may beused include polyglycerol polyricinoleate (PGPR), ammonium salts ofphosphatidic acid (e.g. YN), sucrose esters, oat extract, etc., and anyemulsifying agent or combination, thereof, found to be suitable inchocolate or similar fat/solid system.

Selected combinations of emulsifying agents have been identified toprovide the confectioneries of the present invention, particularlyreduced-fat confectioneries, having improved rheology overconfectioneries prepared using conventional emulsifying agents.Emulsifying agent combinations that are particularly useful in thepresent invention are combinations of lecithin, sucrose polyerucate(ER-290, sold by Mitsubishi Kasei Corporation, Japan) sucrosepolystearate (sold by Mitsubishi Kasei Corporation, Japan), ammoniumphosphatide, phosphated mono-di-glycerides/diacetyl tartaric acid ofmono-glycerides (PMD/DATEM), or fractionated lecithin, with sucrosepolyerucate and/or polyglycerol polyricinoleate (PGPR-ADMUL Wol, sold byQuest International, Hoffman Estates, Ill.).

Advantageously, the emulsifying agent combinations of polyglycerolpolyricinoleate, sucrose polyerucate, and soy lecithin, offersignificant improvement in the rheology of the chocolates of the presentinvention. Use of these preferred emulsifying agent combinationsprovides the chocolates of this invention having enhanced viscosity andyield value.

When a reduced fat chocolate is prepared, a combination of emulsifyingagents is used, i.e., a base emulsifying agent and a second emulsifyingagent. The base emulsifying agent is added in an amount of less than1.0% by weight, as limited by current U.S. Food and Drug AgencyStandards of Identity. The amount of the base emulsifying agent presentin the reduced-fat chocolates is about 0.1% to about 0.9%, preferablyabout 0.2% to about 0.8%, and more preferably about 0.4% to about 0.6%by weight, based on the total weight of the chocolate. Optionally, themixture of the fat and solid-containing chocolate ingredients may beconched prior to addition of the base emulsifying agent.

Sucrose polyerucate may be used as either the base emulsifying agentand/or as the second emulsifying agent. When used as the secondemulsifying agent, the sucrose polyerucate is present in an amount ofabout 0.4% to about 0.6% by weight, based on the total weight of thereduced fat chocolate. Sucrose polyerucate is particularly usefulbecause it reduces both the plastic viscosity and yield value even whenused at concentrations greater than 1.0% by weight. Sucrose polyerucatemay be present in an amount of less than about 1.0%, e.g. about 0.1% toabout 0.9%, preferably about 0.2% to about 0.6%, and more preferablyabout 0.4% to about 0.5% by weight, based on the total weight of thereduced fat chocolate.

Polyglycerol polyricinoleate (PGPR-Admul WOL from Quest Int'l.) isuseful as the second emulsifying agent. Polyglycerol polyricinoleate,which is the partial polyglyceryl ester of inter-esterified castor oilfatty acids, has proven very useful in modifying the yield value ofhigh-viscosity chocolates. The PGPR may be present in amount of about0.05% to about 0.5%, preferably about 0.2% to about 0.35%, based on thetotal weight of the low fat chocolate.

The use of very small amounts of PGPR provides significant benefits. Thecombination of PGPR (0.5% by weight) with lecithin (0.5% by weight)reduces the yield value to zero. When the second emulsifying agent ispolyglycerol polyricinoleate, it is present in an amount of about 0.2%to about 0.35% by weight, based on the total weight of the reduced fatchocolate.

When there is 20% total fat, the PGPR concentration can be as low as0.05% by weight. When the reduced fat chocolate contains less than 23%by weight total fat, the PGPR, in combination with a base emulsifyingagent, may be about 0.05% to about 0.5% by weight. Preferably, PGPR incombination with a base emulsifying agent may be present in an amount ofabout 0.2% to about 0.35% by weight, based on the total weight of thereduced fat chocolate

The rheology of reduced-fat chocolates may be further improved by theuse of a three component emulsifier combination. The addition of sucrosepolyerucate (0.2% by weight) and PGPR (0.2% by weight) reduced the yieldvalue over 70% of a reduced fat chocolate containing 0.6% by weightlecithin and reduced the plastic viscosity over 45%, compared to thelecithin containing reduced fat chocolate.

The preferred emulsifying agent combinations include the combinations oflecithin-sucrose polyerucate, lecithin-polygrycerol polyricinoleate,sucrose polyerucate-polyglycerol polyricinoleate, and lecithin-sucrosepolyerucate-polyglycerol polyricinoleate. Use of these preferredemulsifying agent combinations provides reduced-fat chocolates having atotal fat content below 23% by weight, viscosity values of less than 100poise, and yield values of less than 150 dynes/cm².

As used herein, the term “antioxidant compound” refers to compounds thatprevent oxidation and function as a reducing agent or as an electrondonor/receptor. According to their mode of action, antioxidants may beclassified as free radical terminators, metal ion chelators, or asoxygen scavengers that react with oxygen. Suitable antioxidant compoundclasses include tannins, including condensed tannins and hydrolyzabletannins, quinones, polyhydroxy compounds, phospholipids, tocol compoundsor derivatives thereof. Exemplary antioxidants include, but are notlimited to, The antioxidants also include reducing agents including suchdiverse materials as organic acids, such as ascorbic acid, stannouschloride, and tocopherols (vitamin E). Sulfur dioxide, a preservative,can also function as an antioxidant. Di-lauryl thiodipropionate andthiodipropionic acid can function as preventive antioxidants by reactingwith hydroperoxides.

As used herein, the term “flavoring agent” refers to flavored compoundsor compositions used in food products and confectionery, particularly inchocolates, to impart a desired taste and aroma. A flavoring agent thatis suitable for use as a pre-treatment ingredient is a flavor compoundor composition that demonstrates an activity that prevents reaction,complexation, decomposition or adverse interaction of cocoa polyphenolswith any of the other ingredients used in the preparation of theseproducts or with any polyphenol-reactive material generated from or bythe other ingredients during the preparation of these produces.Exemplary flavoring agents suitable for use as pre-treatment ingredientsinclude vanillin, spices, and naturally expressed citrus or spice oils,which contain flavanoids and phenol-based flavorants, e.g. eugenol,which may function as a free radical terminator and may thus preventreaction of cocoa polyphenols with any free radical species generatedduring production.

Chocolate used in foods in the United States is subject to a standard ofidentity established by the U.S. Food and Drug Administration under theFederal Food, Drug and Cosmetic Act that sets out the requisiteingredients, and proportions thereof, of a confection to permitlabelling of the confection as a “chocolate.” The most popular chocolateor chocolate candy consumed in the United States is in the form of sweetchocolate or milk chocolate. Chocolate is essentially a mixture ofsolid-containing ingredients, including cocoa solids, suspended in fat.Milk chocolate is a confection which contains milk solids, milk fat,chocolate liquor, a nutritive carbohydrate sweetener, cocoa butter andmay include a variety of other ingredients such as emulsifying agents,flavorings and other additives. Crumb chocolate is a type of milkchocolate, containing the same ingredients, however, wet milk andcarbohydrate sweetener ingredients are pre-combined then co-dried, atelevated temperatures, to form a milk crumb that is then used to preparethe milk chocolate. Sweet chocolate contains higher amounts of chocolateliquor, but lower amounts of milk solids than milk chocolate. Semisweetchocolate requires at least 35% by weight chocolate liquor and isotherwise similar in definition to sweet chocolate. Dark chocolate,generally containing only chocolate liquor, a nutritive carbohydratesweetener and cocoa butter, is by definition either a sweet chocolate ora semisweet chocolate. Buttermilk chocolate and skim milk chocolatediffer from milk chocolate in that the milk fat comes from various formsof sweet cream buttermilk and skim milk, respectively. Skim milkrequires the total amount of milk fat to be limited to less than theminimum for milk chocolate. Mixed dairy product chocolates differ frommilk chocolate in that the milk solid includes any or all of the milksolids listed for milk chocolate, buttermilk chocolate or skim milkchocolate. White chocolate differs from milk chocolate in that itcontains no non-fat cocoa solids. Non-standardized chocolates are thosechocolates which have compositions which fall outside the specifiedranges of the standardized chocolates. Chocolates are classified as“non-standardized” chocolates when a specified ingredient is replaced,either partially or completely, such as when the ingredient cocoa butteris replaced with vegetable oils or fats. Any additions or deletions to achocolate recipe made outside the US FDA standards of identity forchocolate will prohibit use of the term “chocolate” to describe theconfectionery. However, as used herein, the term “chocolate” refers toany standard of identity or non-standard of identity chocolate.

The reduced fat chocolates comprise a fat, solid-containing chocolateingredients, and a combination of a base emulsifying agent and at leastone other emulsifying agent. The chocolates are prepared by mixing thefat and chocolate ingredients, adding the base emulsifying agent to themixture, and then adding at least one other emulsifying agent. When theemulsifying agent combination comprises more than two emulsifyingagents, the third emulsifying agent is typically added after the secondemulsifying agent. Any emulsifying agents added after the baseemulsifying agent may be added in any order. The use of combinations ofthe emulsifying agents aids in dispersing the fat. The resultingconfectioneries have the texture of a full-fat confectionery. Thereduced fat chocolates are suitable for use in enrobing, extruding, ormoulding operations. The chocolates have yield values of less than 250dynes/cm², preferably less than 180 dynes/cm², more preferably less than140 dynes/cm², and viscosities of less than 150 poise, preferably lessthan 100 poise, more preferably less than 75 poise.

Chocolate may take the form of solid pieces of chocolate, such as barsor novelty shapes, and may also be incorporated as an ingredient ofother, more complex confections where chocolate is combined with andgenerally coats other foods such as caramel, peanut butter, nougat,fruit pieces, nuts, wafers, ice cream or the like. These foods arecharacterized as microbiologically shelf-stable at 65°-85° F. (18-29°C.), under normal atmospheric conditions.

The term “carbohydrate” refers to nutritive carbohydrate sweeteners,with varying degrees of sweetness intensity that are useful in thepresent invention, may be any of those typically used in the art andinclude, but are not limited to, sucrose, (e.g., from cane or beet),dextrose, fructose, lactose, maltose, glucose syrup solids, corn syrupsolids, invert sugar, hydrolyzed lactose, honey, maple sugar, brownsugar, molasses and the like.

The food products of the present invention may additionally containother ingredients such as milk solids, cocoa solids (cocoa powder),sugar substitutes, natural and artificial flavors (e.g., spices, coffee,salt, brown nut-meats, etc., as well as mixtures of these), proteins,and the like.

Sugar substitutes may be used to partially replace the nutritivecarbohydrate sweetener, particularly in the production ofreduced-calorie confectioneries and chocolates. As used herein, the term“sugar substitute” includes high potency sweeteners, sugar alcohols(polyols) and bulking agents, or combinations thereof. The high potencysweeteners include aspartame, cyclamates, saccharin, acesulfame,neo-hesperidin dihydrochalcone, sucralose, alitame, stevia sweeteners,glycyrrhizin, thaumatin, and the like, and mixtures thereof. Thepreferred high potency sweeteners include aspartame, cyclamates,saccharin, and acesulfame-K. Examples of sugar alcohols may be any ofthose typically used in the art and include sorbitol, mannitol, xylitol,maltitol, isomalt, lactitol and the like. The food products of thepresent invention may also contain bulking agents, typically used incombination with high potency sweeteners. The term “bulking agents” asdefined herein may be any of those typically used in the art and includepolydextrose, cellulose and its derivatives, maltodextrin, gum arabic,and the like.

The term “fermentation factor” is a numerical quantification of thelevel of fermentation of a batch of cocoa beans. Fermentation factorsrange from 100 (under/unfermented) to 400 (fully fermented). To assessthe degree of fermentation, cocoa beans are typically subjected to astandard cut test for assessing quality as defined in industry gradestandards. The bean halves are laid out on a board for visual inspectionof color as well as defects which can arise during bean fermentation,drying and/or storage. Beans can be divided into four fermentationcategories according to their color and appearance: (a) fully fermented,e.g., predominantly a brown hue; (b) partially fermented, e.g.,purple/brown; (c) purple (under-fermented); and (d) slaty (veryunder-fermented and/or unfermented beans). Purple/brown beans includeall beans showing any blue, purple or violet color on the exposedsurface, whether suffused or as a patch. Purple beans should include allbeans showing a completely blue, purple or violet color over the wholeexposed surface. This should also include, irrespective of color, anybeans which are slaty, but not predominantly so (wherein predominantly,in this context, means more than half).

The “fermentation factor” is determined using a grading system forcharacterizing the fermentation of the cocoa beans. Slaty, beingunder/unfermented, is designated as 1, purple as 2, purple/brown as 3and brown as 4. The percentage of beans falling within each category ismultiplied by the weighted number. Thus, the “fermentation factor” for asample of 100% brown beans would be 100×4 or 400, whereas thefermentation factor for a sample of 100% purple beans would be 100×2 or200. A sample of 50% slaty beans and 50% purple beans would have afermentation factor of 150 [(50×1)+(50×2)]. Cut tests applicable tococoa beans derived from the Trinitario and Forastero types may or maynot be applicable to cocoa beans derived from the Criollo type, forexample, where bean color variation ranging from fully purple to lighttan can be encountered. Accordingly, the cut test based on color wouldnot be applicable to specific cocoa genotypes lacking the anthocyaninpigments responsible for the purple color, such as the Catango (orCatongo) type whose beans are light tan in color. Other exceptionsinclude “cocoa beans” derived from other Theobroma species, the Herraniaspecies and their inter- and intra-specific crosses. The beans fromthese species are “tan” in color. For these types of beans the level offermentation may be determined using a modified standard cut test. Usingthe modified test, the surface of the bean (halved) is inspected for thedegree of lines, fissures or cracks which form during fermentation,rather than the change of color.

FIGS. 1(a)-(d) illustrate the change in the surface of the cut bean halfduring the fermentation of the cocoa bean. As can be seen from FIGS.1(a)-(d), the number of lines/fissures and the extent to which theyextend across the entire surface of the cut bean half increases as thebean is fermented. FIG. 1(a) depicts the cut bean half of an unfermentedcocoa bean where the surface is relatively smooth. FIGS. 1(b)-(d) depictthe cocoa beans as it is fermented, with FIG. 1(d) illustrating thefully fermented cocoa bean. As the cocoa bean is fermented, the surfacedevelops small branch-like lines or fissures. This modified test canalso be used to approximate the fermentation factor wherein a cocoa beancorresponding to FIG. 1(a) is designated as 100, FIG. 1(b) as 200, FIG.1(c) as 300 and FIG. 1(d) as 400. While the definitions of theaforementioned categories are a general guide, the assessment accordingto these categories is well within the skill of the ordinary skilledartisan well versed in chocolate and cocoa processing (see Wood et al.,Cocoa, 4th Ed. (1985), incorporated herein by reference, especiallypages 511 to 513). The numerical index, 1-4 or 100-400, are qualitativeterms that are used herein to reflect the relative fermentaiton of cocoabeans and therefore related to the relative concentration of cocoapolyphenols in cocoa beans. A value of 1 or 100 would reflectunfermented beans possessing the highest relative concentration of cocoapolyphenols, that is, the total amount or nearly the total amount ofcocoa polyphenols produced by the cocoa plant in the cocoa bean. A valueof 4 or 400 would reflect fully fermented beans possessing the relativelowest concentration of cocoa polyphenols, that is, the remaining amountof cocoa polyphenols that did not react, decompose, or otherwisetransform under fermentation, roasting, alkalization or other processingprocedures. The actual cocoa polyphenol concentration of any cocoa beansample or cocoa ingredient may be determined using the high performanceliquid chromatographic (HPLC) technique described in Romanczyk, et al.,U.S. Pat. No. 5,554,645.

The term “significant amount” means an amount which maintains the basiccharacteristics of the specified ingredients or composition or product.

The term “fair average quality cocoa beans” refers to cocoa beans thathave been separated from the pulp material and dried and are relativelyfree of mold and infestation. Such beans are a commercial commodity andform the feedstock for the next step in the production processes, e.g.,infra-red heating, roasting, pressing, etc. The term includes any suchbean that has been genetically modified or produced.

The term “raw freshly harvested cocoa beans” refers to seeds or beansfreshly harvested from the cocoa pod and which have not been subjectedto processing other than separation from the pulp. The term includes anysuch bean that has been genetically modified or produced.

A preferred embodiment of this invention is a process for providing aconfectionery product having a conserved cocoa polyphenol concentration,comprising:

(a) mixing a carbohydrate ingredient with at least one pre-treatmentingredient to form a confectionery mix,

(b) combining the confectionery mix with at least one ingredientcontaining cocoa polyphenol, and

(c) forming the polyphenol-containing confectionery product, wherein theproduct contains at least about 10% by weight more polyphenol than aproduct prepared without using the pre-treatment process according tostep (a).

Another embodiment of this invention is a process of preparing achocolate product having a conserved concentration of cocoa polyphenol;the process comprises:

(a) mixing at least one ingredient selected from the group consisting ofmilk ingredients and carbohydrate ingredients, with at least onepre-treatment ingredient to form a confectionery mix,

(b) combining the confectionery mix with at least one ingredientcontaining cocoa polyphenol,

(c) conching the combined ingredients, and

(d) forming the polyphenol-containing chocolate product, wherein theproduct contains at least about 10% by weight more polyphenol than aproduct prepared without using the pre-treatment process according tostep (a).

In another embodiment of this invention, confectionery products,particularly chocolate products, having a conserved concentration ofcocoa polyphenol, and particularly, cocoa polyphenol oligomers 5-12 maybe prepared using a split milling, or split refining process comprising:

(a) mixing at least one ingredient selected from the group consisting ofmilk ingredients and carbohydrate ingredients, with at least onepre-treatment ingredient to form a confectionery mix,

(b) milling or refining the confectionery mix,

(c) combining the milled confectionery mix with at least one ingredientcontaining cocoa polyphenol and having a particle size equal to or lessthan that desired in the confectionery product or chocolate product,

(d) conching the combined ingredients, and

(e) forming the polyphenol-containing confectionery or chocolateproduct, wherein the product contains at least about 10% by weight morepolyphenol than a product prepared without using the pre-treatmentprocess according to step (a).

In yet another embodiment, chocolates having a strong chocolate flavorand conserved concentrations of cocoa polyphenols, and particularly,cocoa polyphenol oligomers 5-12 may be prepared using a split conchingprocess comprising:

(a) mixing at least one ingredient selected from the group consisting ofmilk ingredients and carbohydrate ingredients, with at least onepre-treatment ingredient to form a confectionery mix,

(b) conching the confectionery mix,

(c) combining at least one ingredient containing cocoa polyphenol withthe conched confectionery mix,

(d) refining, then conching, the resulting mixture, and

(e) forming the polyphenol-containing chocolate product, wherein theproduct contains at least about 10% by weight more polyphenol than aproduct prepared without using the pre-treatment process according tostep (a).

Another embodiment of the split conching process, providing chocolateshaving a strong chocolate flavor and conserved concentrations of cocoapolyphenols, particularly, cocoa polyphenol oligomers 5-12, comprises:

(a) mixing at least one ingredient selected from the group consisting ofmilk ingredients and carbohydrate ingredients, with at least onepre-treatment ingredient to form a confectionery mix,

(b) conching the confectionery mix at a temperature of about 60° C. toabout 90° C.,

(c) cooling the conched confectionery mix to a temperature of about 35°C. to about 50 C.,

(d) combining at least one ingredient containing cocoa polyphenol withthe cooled, conched confectionery mix,

(e) refining, then conching, the resulting mixture, and

(f) forming the polyphenol-containing chocolate product, wherein theproduct contains at least about 10% by weight more polyphenol than aproduct prepared without using the pre-treatment process according tostep (a).

Preferably the polyphenol-containing food products prepared by theprocesses of this invention contain about 15% by weight more cocoapolyphenol than a polyphenol-containing food product prepared withoutusing the pre-treatment process according to step (a); more preferably,the food product of this invention contains about 20% by weight morecocoa polyphenol than a food product prepared without using step (a).The comparative polyphenol-conservation value of 10%, 15% and 20% referto the difference between the conserved concentration of polyphenol in atest sample and the conserved concentration of the polyphenol in acontrol sample. The conserved concentration of polyphenol in a sample,expressed as percentage, is the concentration of polyphenol in thesample, relative to the concentration of polyphenol in a theoreticalsample having 100% conservation. The increased concentration of cocoapolyphenol retained, or conserved, in the food products of thisinvention may be measured by analysis of a single oligomer, such ascocoa polyphenol pentamer, as an indicator of improvement in retention.Significantly, the use of the polyphenol pentamer as the analyticalstandard also provides an indication of the concentration of theprocess-sensitive polyphenol oligomers 5-12 retained, or conserved, inthe food products of this invention.

The food products of this invention contain at least acarbohydrate-containing ingredient or a protein-containing ingredient,or a mixture thereof. According to the processes of this invention, atleast one of these ingredients is mixed first with at least onepre-treatment ingredient. Preferably, if both a carbohydrate-containingingredient and a protein-containing ingredient are present in the foodproduct, both ingredients are mixed with at least one pre-treatmentingredient prior to mixing with the polyphenol-containing ingredient.Optionally, the carbohydrate-containing ingredient, protein-containingingredient, or mixture thereof, may be milled or refined prior to mixingwith at least one pre-treatment ingredient. Alternatively, the mixtureof carbohydrate and/or protein-containing ingredients with thepre-treatment ingredient(s) may be milled or refined after mixing.

Optionally, the protein-containing ingredient may be a milk ingredient.According to the process of the present invention, the process ofpreparing a milk chocolate, having a conserved concentration of cocoapolyphenol, comprises mixing both milk ingredients and carbohydrateingredients with at least one pre-treatment ingredient. Milkingredients, as used herein, include any milk-based ingredient commonlyused in food manufacturing, and particularly, confectionery or chocolatemanufacturing. Exemplary milk ingredients include liquid milk, milkproteins (casein, whey protein), condensed milk, sweetened condensedmilk, evaporated milk, milk crumb, milk powder, re-constituted milk,malted milk, malted milk powder, cultured milk powders, and the like.

Preferably, in each of the above-described processes of this invention,the pre-treatment ingredient is selected from the group consisting offat, an emulsifying agent, a cocoa ingredient, an antioxidant compound,a flavoring agent and mixtures thereof. The pre-treatment fat ingredientmay be selected from any fat described hereinabove, but is preferablycocoa butter. The pre-treatment emulsifying agent ingredient may beselected from any emulsifying agent described hereinabove, but ispreferably lecithin, fractionated lecithin, or mixtures thereof. Thepre-treatment cocoa ingredient may be any cocoa ingredient describedhereinabove, but is preferably obtained from cocoa beans having afermentation factor of 300 or greater. The pre-treatment antioxidant andflavoring agent ingredients may be any of the above-describedantioxidant and flavoring agent ingredients.

Preferably, in each of the above-described processes of this invention,the pre-treatment ingredient is a mixture of fat and an at least oneemulsifying agent. More preferably, the pre-treatment ingredient is amixture of lecithin and cocoa butter.

In each of the above-described processes of this invention, thepolyphenol-containing ingredient may be selected from the groupconsisting of a cocoa ingredient comprising procyanidins, an extract ofcocoa beans or a cocoa ingredient comprising procyanidins, synthesizedderivatives of the extracts of cocoa beans or a cocoa ingredientcomprising procyanidins, synthesized cocoa polyphenol compounds, andsynthesized derivatives of synthesized cocoa polyphenol compounds. Thepolyphenol-containing cocoa ingredient is preferably a cocoasolids-containing material derived from shell-free cocoa nib andincludes chocolate liquor and partially or fully defatted cocoa solids(e.g., cake or powder), and the like. Advantageously, thepolyphenol-containing cocoa ingredient is obtained from cocoa beanshaving a fermentation factor less than 300; preferably, the cocoaingredient is obtained from cocoa beans have a fermentation factor lessthan 275, more preferably, from cocoa beans have a fermentation factorless than 250;, more preferably, from cocoa beans have a fermentationfactor less than 225, even more preferably, from cocoa beans have afermentation factor less than 200, more preferably, from cocoa beanshave a fermentation factor less than 150, and most preferably, fromcocoa beans have a fermentation factor less than 125.

A preferred embodiment of this invention is a process for providing adark chocolate having a conserved cocoa polyphenol concentration,comprising:

(a) mixing a carbohydrate nutritive sweetener with lecithin and cocoabutter to form a confectionery mix,

(b) combining the confectionery mix with a chocolate liquor obtainedfrom cocoa beans having a fermentation factor less than 300, and

(c) forming the polyphenol-containing dark chocolate, wherein thechocolate contains at least about 10% by weight more polyphenol than adark chocolate prepared without using the pre-treatment processaccording to step (a).

A preferred embodiment of this invention is a process for providing amilk chocolate having a conserved cocoa polyphenol concentration,comprising:

(a) mixing a milled or refined carbohydrate nutritive sweetener and amilled or refined milk powder with lecithin and cocoa butter to form aconfectionery mix,

(b) combining the confectionery mix with a chocolate liquor obtainedfrom cocoa beans having a fermentation factor less than 300, and

(c) forming the polyphenol-containing milk chocolate, wherein thechocolate contains at least about 10% by weight more polyphenol than amilk chocolate prepared without using the pre-treatment processaccording to step (a).

In a preferred embodiment, at least two cocoa ingredients having varyingconcentrations of cocoa polyphenols are used to prepare the foodproducts and confectionery products of this invention. For example, afirst cocoa ingredient, derived from fermented cocoa beans having afermentation factor of 300 or greater (having a low cocoa polyphenolsconcentration, but a high chocolate flavor/aroma content) may be usedeither as the pre-treatment ingredient, or in combination with otherpre-treatment ingredients. A second cocoa ingredient, derived fromunder-fermented beans having a fermentation factor less than 300 (havinga higher cocoa polyphenols concentration, but a lower chocolateflavor/aroma content) may be used as the polyphenol-containing cocoaingredient. The use of such a cocoa-ingredient blend allows for theproduction of a chocolate having strong flavor/aroma characteristics aswell as enhanced concentrations of cocoa polyphenols.

In another embodiment of this invention, the ingredient containing cocoapolyphenol may be a combination of chocolate liquor and cocoa powder,wherein the liquor and powder are obtained from cocoa beans having afermentation factor less than 300. Preferably, the chocolate liquor andcocoa powder are obtained from cocoa beans having a fermentation factorless than 275, more preferably, from cocoa beans having a fermentationfactor less than 250, more preferably, from cocoa beans having afermentation factor less than 225, even more preferably, from cocoabeans having a fermentation factor less than 200, more preferably, fromcocoa beans having a fermentation factor less than 150, and mostpreferably, from cocoa beans having a fermentation factor less than 125.

Additionally, each of the above-described processes may further comprisethe step of adding a second emulsifying agent, which may be added eitherduring or after conching. The second emulsifying agent may be selectedfrom any of the above-described emulsifying agents. Preferably, thesecond emulsifying agent may be lecithin, sucrose polyerucate, ammoniumphosphatide, polyglycerol polyricinoleate, phosphated mono-anddi-glycerides/di-acetyl tartaric acid of mono-glycerides (PMD/DATEM),fractionated lecithin, or mixtures thereof.

Accordingly, a novel chocolate of the present invention, having a highcocoa polyphenol concentration, may be prepared according to any of theabove-described process further comprising the step of combining theconfectionery mix with a chocolate liquor and a cocoa powder. The novelchocolate may be prepared by the process comprising the steps of:

(i) combining carbohydrate or carbohydrate and milk ingredients with apre-treatment ingredient comprised of lecithin and optionally, at leastone ingredient selected from the group consisting of a fat, a cocoaingredient, an antioxidant compound and a flavoring agent,

(ii) using a combination of a chocolate liquor and a cocoa powder as thepolyphenol-containing ingredient, and

(iii) adding a second emulsifying agent either during or after conching,and

(iv) forming the polyphenol-containing chocolate, wherein the chocolatecontains at least about 10% by weight more cocoa polyphenol than apolyphenol-containing chocolate prepared without using the pre-treatmentprocess according to step (i).

Another embodiment of the invention relates to a food product, and aprocess of preparing the product, having enhanced concentrations ofcocoa polyphenols derived from a cocoa polyphenol-containing ingredient.Preferred cocoa polyphenol-containing ingredients may be selected fromthe group consisting of extracts of cocoa beans or a cocoa ingredientcomprising procyanidins, synthesized derivatives, synthesized cocoapolyphenol compounds, and synthesized derivatives of synthesized cocoapolyphenol compounds. The polyphenol ingredient may be mixed with otherproduct ingredients during the processing, but is preferably mixed withother ingredients at or near the end of processing, or added to theproduct after processing (i.e., spraying onto the product).

Preferably the polyphenol-containing food products prepared by theprocesses of this invention contain about 15% by weight more cocoapolyphenol than a polyphenol-containing product prepared without usingthe pre-treatment process according to step (a); more preferably, thefood products of this invention contain about 20% by weight more cocoapolyphenol than a food product prepared without using step (a). Thepercentage improvement of cocoa polyphenol concentration, as definedherein, may be measured using a single oligomer, such as pentamer, as anindicator of improvement in retention.

Novel food products containing cocoa polyphenols, particularly enhancedconcentrations of cocoa polyphenols, may be prepared by any of theabove-described processes. The novel products are distinguishable fromconventional products either because (1) the inventive products containelevated concentrations of cocoa polyphenols relative to comparativeconventional products (i.e., chocolates, chocolate-flavored confections,etc.) and/or (2) the inventive products contain cocoa polyphenols incontrast to comparative products which do not contain cocoa polyphenols(i.e., rice cakes, edible foods without chocolate flavor/aroma, etc.).

One embodiment of this invention relates to a food product containing acocoa polyphenol ingredient. Preferably, the product comprises at least1 μg cocoa polyphenols per gram product, preferably at least 2 μg, morepreferably at least 5 μg, and most preferably at least 10 μg cocoapolyphenols per gram product. According to one preferred embodiment, theproduct comprises at least 25 μg cocoa polyphenols per gram product,preferably at least 50 μg, more preferably at least 100 μg, and mostpreferably at least 150 μg cocoa polyphenols per gram product.

Another embodiment of the invention relates to a chocolate comprising atleast 3,600 μg cocoa polyphenol per gram chocolate, preferably at least4,000 μg, advantageously at least 4,500 μg, more preferably at least5,000 μg, and most preferably at least 5,500 μg cocoa polyphenols pergram chocolate. According to one preferred embodiment, the chocolatecontains at least 6,000 μg cocoa polyphenols per gram chocolate,preferably at least 6,500 μg, more preferably at least 7,000 μg, andmost preferably at least 8,000 μg cocoa polyphenols per gram chocolate.

Another embodiment of the invention relates to a chocolate comprising atleast 100 μg cocoa polyphenol pentamer per gram chocolate, preferablythe chocolate contains at least 150 μg, preferably the chocolatecontains at least 200 μg, preferably the chocolate contains at least 250μg, preferably the chocolate contains at least 300 μg, more preferably,at least 325 μg, and most preferably, at least 350 μg cocoa polyphenolpentamer per gram chocolate. According to one preferred embodiment, thechocolate contains at least 375 μg cocoa polyphenol pentamer per gramchocolate, preferably, at least 400 μg, more preferably at least 425 μg,and most preferably, at least 450 μg cocoa polyphenol pentamer per gramchocolate.

Yet another embodiment of the invention relates to a milk chocolatecontaining milk solids and comprising at least 1,000 μg cocoapolyphenols per gram chocolate, preferably at least 1,250 μg, morepreferably at least 1,500 μg, and most preferably at least 2,000 μgcocoa polyphenols per gram chocolate. According to one preferredembodiment, the milk chocolate contains at least 2,500 μg cocoapolyphenols per gram chocolate, preferably at least 3,000 μg, morepreferably at least 4,000 μg, and most preferably at least 5,000 μgcocoa polyphenols per gram chocolate.

Another embodiment of the invention relates to a milk chocolatecontaining milk solids and comprising at least 85 μg cocoa polyphenolpentamer per gram chocolate, preferably at least 90 μg, more preferablyat least 100 μg, and most preferably at least 125 μg cocoa polyphenolpentamer per gram chocolate. According to one preferred embodiment, themilk chocolate contains at least 150 μg cocoa polyphenol pentamer pergram chocolate, preferably at least 175 μg, more preferably at least 200μg, and most preferably at least 250 μg cocoa polyphenol pentamer pergram chocolate.

The Examples which follow are intended as an illustration of certainpreferred embodiments of the invention, and no limitation of theinvention is implied. In the following Examples 3-9, the “fat” may becocoa butter or mixtures of cocoa butter and milk fat. The milk fat maybe used in a concentration, as desired, to provide a finished chocolatehaving a preferred hardness and snap. In the following Examples 3-9, the“CP Liquor” and “CP Cocoa Powder” are cocoa polyphenol-containingchocolate liquor and cocoa polyphenol-containing cocoa powder,respectively, obtained from cocoa beans having a fermentation factor ofless than 300.

EXAMPLE 1 Method of Obtaining Cocoa Polyphenol Cocoa Solids from CocoaBeans

Commercially available cocoa beans having an initial moisture content offrom about 7 to 8 percent by weight were pre-cleaned using an 11″×56″Scalperator (manufactured by Carter Day International, Minneapolis,Minn., USA). Approximately 600 bags of cocoa beans (39,000 kg) werepre-cleaned over a 6.5 hour time period. The beans were fed into theinlet hopper where the flow rate was regulated by a positive feed roll.

The beans were fed onto the outside of a rotating wire mesh scalpingreel. The beans passed through the wire mesh reel and subsequentlythrough an air aspiration chamber where light dirt, dust and stringswere aspirated out of the product stream. The beans that did not passthrough the scalping reel were conveyed to the reject stream. Thisreject stream consisted of large clumps of beans, sticks, stones, etc.The amount of resultant reject was approximately 150 kg, or 0.38% of thestarting material. The resulting pre-cleaned product weighed about38,850 kg and was passed to the bean cleaning step.

The pre-cleaned bean products from the Scalperator were then furthercleaned using a Camas International SV4-5 Air Fluidized Bed DensitySeparator (AFBDS, manufactured by Camas International, Pocotello, Ind.,USA). About 38,850 kg of cocoa bean products were fed into the AFBDSover a time period of about 6.5 hours. The apparatus removedsubstantially all heavy impurities such as stones, metal, glass, etc.from the beans, as well as lighter unusable materials such as moldy andinfested cocoa beans, resulting in a cleaned bean product whichcontained substantially only usable cocoa beans. The resulting heavyimpurities removed weighed about 50 kg and the light unusable materialsweighed about 151 kg. A total of about 38,649 kg of cleaned beans wasobtained after both the pre-cleaning and cleaning steps describedhereinabove (99.1% yield after cleaning).

The cleaned cocoa beans were then passed through a infra-red heatingapparatus. The apparatus used was the Micro Red 20 electric infra-redvibratory Micronizer (manufactured by Micronizing Company (U.K.)Limited, U.K.). The Micronizer was run at a rate of about 1,701kilograms per hour. The depth of beans in the vibrating bed of theMicronizer was about 2 inches or about 2-3 beans deep. The surfacetemperature of the Micronizer was set at about 165° C., therebyproducing an internal bean temperature (IBT) of about 135° C. in a timeranging from 1 to 1.5 minutes. This treatment caused the shells to dryrapidly and separate from the cocoa nib. Since substantially all of thecocoa beans fed into the Micronizer were whole beans and weresubstantially free of small broken pieces of bean or shell, no sparks orfires were observed during the infra-red heating step. The broken piecesseparated by the vibrating screen prior to the Micronizer werere-introduced into the product stream prior to the winnowing step.

The beans after the Micronizer had a moisture content of about 3.9% byweight. The beans emerged from the Micronizer at an IBT of about 135° C.and were immediately cooled to a temperature of about 90° C. in aboutthree minutes to minimize additional moisture loss. The total beansavailable after the heating step was about 36,137 kg.

The beans were then subjected to winnowing using a Jupiter Mitra Seitawinnower (manufactured by Jupiter Mitra Seita, Jakarta, Indonesia). Thewinnowing step cracked the beans to loosen the shells and separated thelighter shells from the nibs while at the same time minimizing theamount of nib lost with the shell reject stream. The feed rate into thewinnower was about 1,591 kg per hour. The resultant products includedabout 31,861 kg of usable nibs and 4,276 kg of reject shells. Theoverall yield of usable nibs from starting material was about 81.7%.

The resulting cocoa nibs were pressed using a Dupps 10-6 Pressor(manufactured by The Dupps Company, Germantown, Ohio, USA). A steady,consistent feed of about 1,402 kg per hour of nibs was fed into twoscrew presses to extract butter. The press produced about 16,198 kg ofcocoa butter which contained about 10% cocoa solids, and about 15,663 kgof cocoa solids which contained about 100n butter.

The cocoa butter was further processed using a Sharples P3000 decantingcentrifuge (manufactured by Jenkins Centrifuge Rebuilders, N. KansasCity, Mo., USA). Centrifugation reduced the solids content in the butterto about 1-2% solids and provided about 13,606 kg of butter and 2,592 kgof cocoa solids containing about 40 to 45% butter. The butter containing1-2% solids was further processed using a plate and frame filter(manufactured by Jupiter Mitra Seita) which removed the remaining solidsfrom the butter and provided about 13,271 kg of clear cocoa butter andabout 335 kg of cocoa solids containing 40-45% butter.

The cocoa solids removed from the centrifuge and the filter presscontained about 40-45% fat and were pressed in a batch hydraulic pressto produce 10% fat cocoa cake. This material produced about 1,186 kg ofclear butter and 1,742 kg of cocoa solids.

The total clear butter yield from the incoming beans was 14,456 kg, or37.1%. The total cocoa solids produced from the incoming beans was17,405 kg, or 44.6%.

Analysis of the actual cocoa polyphenol content of the cocoa beans andcocoa-containing products produced therefrom, may be conducted using thehigh performance liquid chromatographic (HPLC) technique described inRomanczyk, et al., U.S. Pat. No. 5,554,645. A sample of cocoa powder,produced according to the above-described process from unfermented cocoabeans (fermentation factor 100), was analyzed according to theabove-referenced method and shown to contain the following polyphenolconcentrations: a total polyphenol concentration of 32,743 μg ofpolyphenol per gram of cocoa powder, a monomer concentration of 9,433μg/g, a dimer concentration of 5,929 μg/g, trimer concentration of 5,356μg/g, tetramer concentration of 4,027 μg/g, pentamer concentration of3,168 μg/g, hexamer concentration of 2,131 μg/g, heptamer concentrationof 1,304 μg/g, octamer concentration of 739 μg/g, nonamer concentrationof 439 μg/g.

EXAMPLE 2 Production of Chocolate Liquor Containing Cocoa Polyphenols

Fair average quality (FAQ) cocoa beans having an initial moisturecontent 7.4% by weight and a fermentation factor level of 233 (31%slaty, 29% purple, 22% purple brown and 17% brown) were selected as thestarting material. The cocoa beans were then passed through an infra-redheating apparatus. The apparatus used was an infra-red vibratingmicronizer (manufactured by Micronizer Company (U.K.) Limited, U.K.).The feed rate of beans through the infra-red heater and the infra-redheater bed angle were varied to control the amount of heat treatment thebeans received. The amount of time the beans spent in the infra-redheater (residence time) was determined by the bed angle and the feedrate. The times used to prepare the example material are listed in theTable 1 below. At the outlet of the micronizer the IBT of the beans wasmeasured, these values are also shown in Table 1.

A 1 kg sample of infra-red heated beans, collected off the infra-redheater at different IBTs, were cracked into smaller pieces. This is doneto facilitate the separation of the nib from the shell. The laboratorypiece of equipment used to remove the shell was the Limiprimita CocoaBreaker made by the John Gordon Co. LTD. of England. The cracked beanswere next passed through a laboratory scale winnowing system, using aCatador CC-1 manufactured by the John Gordon Co. LTD, England.

The cocoa nibs were next milled into a coarse liquor using a Melangemade by Pascall Engineering Co. LTD, England. This device crushes andgrinds the nibs into a chocolate liquor. The normal operatingtemperature for the liquor in the Melange in approximately 50° C. Thissame process of taking nibs to a coarse liquor could be done on a largerproduction scale using other types of mills, such as a Carle & MontanariMill. The cocoa nibs were ground in the Melange for one hour. Theconcentration of cocoa polyphenols was measured for the samples relativeto the infra-red heated temperatures. These values are contained in theTable 1 below.

TABLE 1 Residence % Moisture μg/g Pentamer μg/g Of Total Time in in inPolyphenols Micronizer, Finished Defatted in Defatted IBT° C. SecondsLiquor Liquor Liquor 107 42 3.9 3,098 39,690 126 82 1.87 1,487 28,815148 156  1.15   695 23,937

EXAMPLE 3 Control Sample

A standard chocolate batch process using a 10 lb. Sigma blade mixer(manufactured by Teledyne Read Co., York, Penn.) was used to mixtogether the following ingredients.

% Concentration Ingredient (by weight) Sucrose  40% Chocolate Liquor  7% CP Liquor  49% Fat 3.5% Lecithin 0.5%

The ingredients were added into a 10 lb. Sigma blade mixer (manufacturedby Teledyne Read Co., York, Penn.), in order of chocolate liquor and CPliquor, sucrose, cocoa butter, and flavorings. The resulting batch ofingredients was mixed until homogeneous, at about 35° C. to about 90° C.The CP liquor, prepared according to Example 2, used to prepare thechocolate samples contained 1150 μg polyphenol pentamer per gram of CPliquor. The mixture was refined to a micrometer particle size of 20microns, conched and standardized (adjustment of viscosity and/or fatcontent to obtain chocolate with desired properties). The samples wereanalyzed for cocoa polyphenol concentration using the high performanceliquid chromatographic (HPLC) technique described in Romanczyk, et al.,U.S. Pat. No. 5,554,645 after mixing or after standardization.

EXAMPLE 4

Test chocolates were prepared using the same recipe and ingredients asExamples 3. The lecithin and fat were combined and mixed, using a 10 lb.Sigma blade mixer until homogeneous. The resulting fat/lecithin mixturewas added to the granulated sucrose in a second 10 lb. Sigma mixer. Thesucrose, fat and lecithin were mixed at about 35° C. to about 90° C.until homogeneous. The remaining ingredients, including the chocolateliquor having a high cocoa polyphenol concentration, were added andmixed until homogeneous. The resulting mixture was refined to amicrometer particle size of about 20 microns, conched, standardized andanalyzed for cocoa polyphenol concentrations as in Example 3.

Table 2 lists the comparative results from a set of chocolates preparedaccording to the processes described in Examples 3 (Control) and 4(Test). The chocolate liquor, used to prepare these chocolates,contained 1150 μg polyphenol pentamer per gram of chocolate liquor.Assuming 100% conservation of polyphenol concentration, the chocolateswould contain 570 μg of polyphenol pentamer per gram of chocolate.Pentamer concentration of the Test samples was determined directly afterinitial batch mixing.

TABLE 2 Pentamer % Increased Sample (μg) Conservation Control-1 361Test-1 418   10% Control-2 360 Test-2 472 19.6% Control-3 313 Test-3 38512.6%

Each test sample showed at least about a 10% by weight increase inpolyphenol concentration over the control sample.

EXAMPLE 5

A control and test chocolate were prepared using the same ingredientsand in a manner substantially similar to Examples 3 and 4, except thatthe concentration of lecithin was increased to 0.75% by weight. Pentamerconcentration of these chocolates was measured after standardization(finished chocolate). The chocolate sample prepared according to theabove test process contained 545.5 μg pentamer per gram of chocolate(95.7% conservation of pentamer), whereas the chocolate preparedaccording to the control process contained 439.6 μg pentamer per gram ofchocolate (77.1% conservation of pentamer). Accordingly, the testchocolate, prepared by the inventive process, retained 18.6% by weightmore cocoa polyphenol pentamer than the control chocolate.

EXAMPLE 6

A control and test dark chocolate were prepared according to theprocesses described in Examples 3 and 4, using the ingredients withinthe concentration ranges set forth below. The selection of theappropriate ingredients and ingredient amounts within the given range toprepare a chocolate is readily performed by one skilled in the art,without undue experimentation.

% Concentration Range Ingredient (by weight) Sucrose 35-55% CP Liquor30-65% Fat  1-35% Lecithin  0.25%

The chocolate liquor used to prepare the chocolates in these Examplescontained 7819 μg total procyanidins per gram of chocolate liquor and1300 μg pentamer per gram of chocolate liquor. The total procyanidincontent represents the total cocoa polyphenol content of the liquor.Assuming 100% conservation of polyphenol concentration, the chocolateswould contain 615 μg polyphenol pentamer per gram of chocolate. The testdark chocolate, prepared according to the process of Example 4,contained 502 μg pentamer (81.6% conservation) and 7091 μg totalprocyanidin (90.6% conservation) per gram of chocolate. The control darkchocolate, prepared according to the process of Example 3, contained 421μg pentamer (68.5% conservation) and 6292 μg total procyanidin (80.5%conservation) per gram of chocolate. Accordingly, the test chocolatesample prepared using the inventive process retained 13.1% by weightmore cocoa polyphenol pentamer and 10.2% by weight more totalprocyanidins than the control chocolate sample.

EXAMPLE 7

Dark chocolates were prepared according to the process described below,using the following general recipe:

% Concentration Range Ingredient (by weight) Sucrose 35-55% ChocolateLiquor 15-30% CP Liquor 10-20% Fat  0-15% Lecithin 0.1-1.0% 

The lecithin and fat were combined and mixed in a Buhler Paste Mixer(sold by Buhler Refiner Co., Minneapolis, Minn.) until homogeneous. Theresulting fat/lecithin mixture was added to the sucrose in Petzholdtconches, models PVW 2000 and PVW 3000 (manufactured by J. S. PetzholdtInh. H. Pilz., Frankfurt, Germany) and mixed at about 35° C. to about90° C. until homogeneous. The remaining ingredients, including thechocolate liquor and the CP liquor were added to thelecithin/fat/sucrose mixture and mixed until homogeneous. The resultingmixture was refined to a micrometer particle size of about 20 microns,conched, standardized and analyzed for cocoa polyphenol concentration asin Example 3.

The combined chocolate liquors used in this Example could provide a darkchocolate containing a total procyanidin concentration of 2933 μg and apentamer concentration of 162 μg per gram of chocolate. Two samples ofthe dark chocolate were prepared according to the above process and weredetermined to contain 158 μg pentamer and 2845 μg total procyanidins and140 μg pentamer and 2866 μg total procyanidins, respectively.

EXAMPLE 8

A dark chocolate was prepared according to the process described below,using the following general recipe:

% Concentration Range Ingredient (by weight) Sucrose 15-35% CP Liquor40-75% CP Cocoa Powder  1-10% Fat  1-10% Vanillin 0.01-0.05%   Lecithin0.1-1.0% 

Using a 10 lb. Sigma blade mixer, the lecithin and fat were combined andmixed until homogeneous. The resulting fat mixture was added to thegranulated sucrose in a second 10 lb. Sigma mixer. The sucrose, fat andlecithin were mixed at about 35° C. to about 90° C. until homogeneous.The remaining ingredients, including the CP liquor and CP cocoa powder,were added and mixed until homogeneous. The resulting mixture wasrefined to a micrometer particle size of about 20 microns, conched,standardized and analyzed for cocoa polyphenol concentration as inExample 3. The chocolate liquor used to prepare the chocolates in thisExample contained a total of 1000 μg pentamer per gram of chocolateliquor and the cocoa powder contained 1700 μg pentamer per gram ofpowder. Assuming 100% conservation of polyphenol concentration, thechocolates prepared according to the recipe above would contain of 768μg polyphenol pentamer per gram of chocolate. This dark chocolatecontained 732 μg pentamer per gram of chocolate, and thus retained over95%, by weight, of the desired polyphenol pentamer present in thepolyphenol pentamer-containing ingredients used to prepare thechocolate.

EXAMPLE 9

A milk chocolate was prepared according to the process described below,using the following general recipe:

% Concentration Range Ingredient (by weight) Sucrose 35-55% MilkIngredient 12-25% CP Liquor 10-20% Fat 15-25% Emuslifier 0.1-1.0% 

At least 21% of the fat and at least 30% of the emulsifier were combinedand mixed until homogeneous, and the resulting fat mixture was added tothe sucrose and milk ingredients, and mixed. The CP liquor was added tothat mixture, and mixed until homogeneous. The resulting mixture wasrefined, conched, standardized by addition of the remaining fat andemulsifier, and analyzed for cocoa polyphenol concentration as inExample 3. Assuming 100% conservation of polyphenol concentration, thechocolate liquor used to prepare this chocolate, would provide a milkchocolate containing 120 μg pentamer per gram of chocolate. The milkchocolate, prepared according to the above process, contained 115 μgpentamer per gram of chocolate, and thus retained over 95%, by weight,of the desired polyphenol pentamer present in the polyphenolpentamer-containing ingredient used to prepare the chocolate.

Other variations and modifications, which will be obvious to thoseskilled in the art, are within the scope and teachings of thisinvention. This invention is not to be limited except as set forth inthe following claims.

What is claimed is:
 1. A process for conserving cocoa polyphenols duringthe processing of one or more cocoa ingredient(s) containing cocoapolyphenols including cocoa procyanidins into a product comprising (i)carbohydrate ingredient(s) (ii) milk ingredient(s), (iii) carbohydrateingredient(s) and milk ingredient(s) ad (iv) the polyphenol-containingcocoa ingredient(s) which are selected from the group consisting ofchocolate liquor, partially defatted cocoa solids, fully defatted cocoasolids, cocoa extract, synthetic cocoa procyanidins, and mixturesthereof, which process comprises the steps of: (a) pretreating thecarbohydrate ingredient(s), the milk ingredient(s), or the carbohydrateingedient(s) and milk ingredient(s) with one or more pretreatmentingredients selected from the group consisting of an antioxidant, anemulsifier, a fat, a flavorant, and mixtures thereof to form a firstmixture; (b) adding the cocoa polyphenol-containing cocoa ingredient(s)to the first mixture to form a second mixture; and (c) processing thesecond mixture into the cocoa-containing product.
 2. The process ofclaim 1, wherein the cocoa ingredients are prepared from cocoa beanshaving a fermentation factor of less than 300, from cocoa beans having afermentation factor of 300 or greater, or from mixtures thereof.
 3. Theprocess of claim 2, wherein the cocoa ingredient(s) are prepared fromcocoa beans having a fermentation factor of less than
 300. 4. Theprocess of claim 2, wherein the cocoa ingredient(s) are prepared fromcocoa beans having a fermentation factor of 300 or greater.
 5. Theprocess of claim 1, wherein the carbohydrate ingredient(s) arecarbohydrate sweetner(s), sugar substitutes, or mixture thereof.
 6. Theprocess of claim 5, wherein the carbohydrate sweetener is selected fromthe group consisting of sucrose, dextrose, fructose, lactose, invertsugar, hydrolyzed lactose, honey, maple sugar, brown sugar, molasses,and mixtures thereof.
 7. The process of claim 6, wherein thecarbohydrate sweetener is sucrose, lactose, or mixtures thereof.
 8. Theprocess of claim 1, wherein the antioxidant is selected from the groupconsisting of tannins, quinones, polyhydroxy compounds, phospholipids,tocol compounds, and derivatives thereof.
 9. The process of claim 1,wherein the emulsifier is selected from the group consisting oflecithin, fractionated lecithin, hydroxylated lecithin, mono-glycerides,di-glycerides, sorbitan monstearate, polyoxyethylene sorbitanmonostearate, lactylated fatty acid esters of glycerol, lactylated fattyacid esters of propylene glycol, polyglycerol esters of fatty acids,propylene glycol monoesters of fats, propylene glycol diesters of fats,propylene glycol monoesters of fatty acids, propylene glycol diesters offatty acids, polyglycerol polyricinoleate, ammonium salts ofphosphatidic acid, sucrose esters, oat extract and mixtures thereof. 10.The process of claim 1, wherein the fat is cocoa butter.
 11. The processof claim 1, wherein the flavorant is vanillin, spices, naturallyexpressed citrus oils, or naturally expressed spice oils.
 12. Theprocess of claim 1, wherein the pretreatment ingredient is a mixture ofthe emulsifier and the fat or a mixture of the antioxidant and the fat.13. The process of claim 12, wherein the emulsifier is lecithin and thefat is cocoa butter.
 14. The process of claim 1, wherein the productfurther comprises alkalized cocoa ingredients.
 15. The process of claim1, further comprising the step of reducing the particle size of thecarbohydrate ingredient(s) and/or the milk ingredient(s) prior to thepretreating step.
 16. The process of claim 1, further comprising thestep of reducing the particle size of the cocoa ingredient(s) prior toadding the cocoa ingredient(s) to the first mixture.
 17. The process ofclaim 1, further comprising the step of reducing the particle size ofthe carbohydrate ingredient(s) and/or milk ingredient(s) prior to thepretreating step and further comprising the step of reducing theparticle size of the cocoa ingredient(s) prior to adding the cocoaingredient(s) to the first mixture.
 18. A fool product prepared by theprocess of claim 1, wherein the product is a food and wherein the cocoaingredient is chocalate liquor or mixtures thereof with partiallydefatted of fully defatted cocoa solids.
 19. The food product of claim18, wherein the food product is a confectionery.
 20. The food product ofclaim 19, wherein the confectionery is a semisweet or sweet chocolate.21. The food product of claim 20, wherein the chocolate is a standard ofindentity chocolate.
 22. The food product of claim 20, wherein thechocolate is a non-standard of indentity chocolate.
 23. The food productof claim 19, wherein the confectionery is a milk chocolate, a buttermilkchocolate, a skim milk chocolate, or a mixed dairy chocolate.
 24. Thefood product of claim 23, wherein the chocolate is a standard ofindentity chocolate.
 25. The food product of claim 23, wherein thechocolate is a non-standard of indentity chocolate.
 26. The food productof claim 19, wherein the confectionery is a white chocolate.
 27. Thefood product of claim 19, wherein the confectionery is a food productwith a chocolate coating.
 28. The food product of claim 19, wherein theconfectionery is a reduced fat chocolate confectionery.
 29. A dietsupplement prepared by the process of claim
 1. 30. A product prepared bythe process of claim 1, wherein the cocoa polyphenol-containingingredient is the cocoa extract.
 31. A product prepared by the processof claim 1, wherein the cocoa polyphenyl-containing ingredient is thesynthetic cocoa procyanidin.